4-Chlorobenzoic Acid → HCID 21837466, compound

HRID 1739814Notes

Reaction equation

HRID 1739814 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[C:11]1([CH:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][C:19](=[O:27])[CH2:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:24]2[CH:25]=[C:26]3[C:21](=[CH:22][CH:23]=2)[NH:20][C:19](=[O:27])[CH2:18][CH:17]3[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 63184-Chlorobenzoic AcidHCID 2725094-Phenyl-3,4-dihydroquinolin-2(1h)-one

Product 1

HCID 21837466HCID 21837466, compoundYield 50.8%

Procedure

4-Chlorobenzoic acid (21.23 g) and 3,4-dihydro-4-phenyl-2(1H)-quinolinone (15 g) were heated in polyphosphoric acid (150 g) at 140° C. for 24 hours. The mixture was poured into ice water and filtered off. The precipitate was taken up in DCM. The organic layer was washed with NaHCO3 (10%) and water, dried (MgSO4) and evaporated. The residue was crystallized from 2-propanone, yielding 12.34 g (50%) of (±)-6-(4-chlorobenzoyl)-3,4-dihydro-4-phenyl-2(1H)-quinolinone; mp. 204° C. (interm. 2-a).

Workup

  1. filtrationfiltered off
  2. washThe organic layer was washed with NaHCO3 (10%) and water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was crystallized from 2-propanone

Sources & evidence

ORD record
ord-3eb43501457542c6b1408ab1a2df7b8d
Source dataset
uspto-grants-1999_10
Patent number
US05968952

Reaction notes

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